tert-butyl (3S)-3-aminopiperidine-1-carboxylate → HCID 89784034, compound
Reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:22][C@H:23]1[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]1>CS(C)=O>[O:21]=[C:15]1[C:14]2[CH:13]=[C:12]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[N:3]=[C:2]([NH:22][C@H:23]3[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]3)[CH:11]=[CH:10]4)[NH:20][C:19]=2[CH2:18][CH2:17][NH:16]1Participants
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 50 mg, 0.168 mmol) and (S)-tert-butyl 3-aminopiperidine-1-carboxylate (Chem-Impex International, Wood Dale, Ill.; 168 mg, 0.840 mmol) in DMSO (0.5 mL) was stirred under argon at 100° C. for 19 h, then at 130° C. for 5 h, then at 150° C. for 17 h. The mixture was cooled to 25° C. and partitioned between DCM (30 mL) and water (20 mL). The organic layer was separated, and the aq. layer was extracted with DCM (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to provide crude (S)-tert-butyl 3-((8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinolin-2-yl)amino)piperidine-1-carboxylate (193.5 mg) as a brown solid (used without further purification in the subsequent transformation): m/z (ESI, +ve) 462.4 (M+H)+.
Workup
- waitat 150° C. for 17 h
- custompartitioned between DCM (30 mL) and water (20 mL)
- customThe organic layer was separated
- extractionthe aq. layer was extracted with DCM (2×20 mL)
- dry with materialThe combined organic extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1885ed0683384aadba0c68ce41d7d64e
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Reaction notes
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